Chapter 26, Problem 26.54P

Interpretation Introduction

Interpretation:

A synthesis of $\text{poly}\left(\text{vinyl amine}\right)$ that involves the polymerization of $\text{N-vinyl formamide}$ is to be proposed. How $\text{poly}\left(\text{vinyl amine}\right)$ can be produced by polymerizing vinyl amine (${\text{H}}_{\text{2}}{\text{C=CH -NH}}_{\text{2}}$) is to be explained.

Concept introduction:

$\text{N-vinyl formamide}$ is a vinyl polymer, so it can be polymerized using $\text{benzoyl peroxide}$ to produce $\text{poly}\left(\text{vinyl formamide}\right)$. The repeating unit of $\text{poly}\left(\text{vinyl formamide}\right)$ has an $\text{O=C-N}$ pendant group, characteristic of an amide. But the repeating unit of $\text{poly}\left(\text{vinyl amine}\right)$ has ${\text{NH}}_2$ pendant group, which releases the $\text{N-}$ containing leaving group as an amine. To carry out this transformation, a nucleophilic addition-elimination is required, which will eliminate the $\text{N-}$ containing portion as a leaving group.